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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2013-01-09 12:11:22 UTC
Update Date2023-02-21 17:29:15 UTC
HMDB IDHMDB0059716
Secondary Accession Numbers
  • HMDB59716
Metabolite Identification
Common Name9-Methylxanthine
Description9-Methylxanthine belongs to the class of organic compounds known as xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety. In another study, 9-Methylxanthine, as a chemical relatives of caffeine, is able to evoke contractures in mammalian heart. 9-Methylxanthine is an extremely weak basic (essentially neutral) compound (based on its pKa). 9-Methylxanthine is a diuretic agent that serves as a smooth muscle relexant and cardiac muscle and CNS stimulant. 9-Methylxanthine is found to be effective in treating apnea in preterm infants (PMID: 11686952 ). Clinically, it is employed as a bronchodilator.
Structure
Data?1677000555
SynonymsNot Available
Chemical FormulaC6H6N4O2
Average Molecular Weight166.1374
Monoisotopic Molecular Weight166.049075456
IUPAC Name9-methyl-2,3,6,9-tetrahydro-1H-purine-2,6-dione
Traditional Namemethylxanthine
CAS Registry NumberNot Available
SMILES
CN1C=NC2=C1NC(=O)NC2=O
InChI Identifier
InChI=1S/C6H6N4O2/c1-10-2-7-3-4(10)8-6(12)9-5(3)11/h2H,1H3,(H2,8,9,11,12)
InChI KeyDHNIKYWYTSMDDA-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassImidazopyrimidines
Sub ClassPurines and purine derivatives
Direct ParentXanthines
Alternative Parents
Substituents
  • Xanthine
  • 6-oxopurine
  • Purinone
  • Alkaloid or derivatives
  • Pyrimidone
  • N-substituted imidazole
  • Pyrimidine
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Vinylogous amide
  • Lactam
  • Urea
  • Azacycle
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
DispositionNot Available
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility6.72 g/LALOGPS
logP-0.56ALOGPS
logP-0.023ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)9.06ChemAxon
pKa (Strongest Basic)0.38ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area76.02 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity40.51 m³·mol⁻¹ChemAxon
Polarizability14.81 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+134.74331661259
DarkChem[M-H]-132.64731661259
DeepCCS[M+H]+127.32930932474
DeepCCS[M-H]-124.56530932474
DeepCCS[M-2H]-161.33130932474
DeepCCS[M+Na]+136.35630932474
AllCCS[M+H]+134.332859911
AllCCS[M+H-H2O]+129.732859911
AllCCS[M+NH4]+138.532859911
AllCCS[M+Na]+139.732859911
AllCCS[M-H]-130.632859911
AllCCS[M+Na-2H]-131.332859911
AllCCS[M+HCOO]-132.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
9-MethylxanthineCN1C=NC2=C1NC(=O)NC2=O2566.9Standard polar33892256
9-MethylxanthineCN1C=NC2=C1NC(=O)NC2=O1826.3Standard non polar33892256
9-MethylxanthineCN1C=NC2=C1NC(=O)NC2=O2254.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
9-Methylxanthine,1TMS,isomer #1CN1C=NC2=C1N([Si](C)(C)C)C(=O)[NH]C2=O1888.7Semi standard non polar33892256
9-Methylxanthine,1TMS,isomer #1CN1C=NC2=C1N([Si](C)(C)C)C(=O)[NH]C2=O2060.6Standard non polar33892256
9-Methylxanthine,1TMS,isomer #1CN1C=NC2=C1N([Si](C)(C)C)C(=O)[NH]C2=O2810.1Standard polar33892256
9-Methylxanthine,1TMS,isomer #2CN1C=NC2=C1[NH]C(=O)N([Si](C)(C)C)C2=O1906.0Semi standard non polar33892256
9-Methylxanthine,1TMS,isomer #2CN1C=NC2=C1[NH]C(=O)N([Si](C)(C)C)C2=O2131.9Standard non polar33892256
9-Methylxanthine,1TMS,isomer #2CN1C=NC2=C1[NH]C(=O)N([Si](C)(C)C)C2=O2836.9Standard polar33892256
9-Methylxanthine,2TMS,isomer #1CN1C=NC2=C1N([Si](C)(C)C)C(=O)N([Si](C)(C)C)C2=O2020.4Semi standard non polar33892256
9-Methylxanthine,2TMS,isomer #1CN1C=NC2=C1N([Si](C)(C)C)C(=O)N([Si](C)(C)C)C2=O2118.9Standard non polar33892256
9-Methylxanthine,2TMS,isomer #1CN1C=NC2=C1N([Si](C)(C)C)C(=O)N([Si](C)(C)C)C2=O2400.4Standard polar33892256
9-Methylxanthine,1TBDMS,isomer #1CN1C=NC2=C1N([Si](C)(C)C(C)(C)C)C(=O)[NH]C2=O2091.9Semi standard non polar33892256
9-Methylxanthine,1TBDMS,isomer #1CN1C=NC2=C1N([Si](C)(C)C(C)(C)C)C(=O)[NH]C2=O2281.0Standard non polar33892256
9-Methylxanthine,1TBDMS,isomer #1CN1C=NC2=C1N([Si](C)(C)C(C)(C)C)C(=O)[NH]C2=O2787.0Standard polar33892256
9-Methylxanthine,1TBDMS,isomer #2CN1C=NC2=C1[NH]C(=O)N([Si](C)(C)C(C)(C)C)C2=O2134.8Semi standard non polar33892256
9-Methylxanthine,1TBDMS,isomer #2CN1C=NC2=C1[NH]C(=O)N([Si](C)(C)C(C)(C)C)C2=O2321.8Standard non polar33892256
9-Methylxanthine,1TBDMS,isomer #2CN1C=NC2=C1[NH]C(=O)N([Si](C)(C)C(C)(C)C)C2=O2823.1Standard polar33892256
9-Methylxanthine,2TBDMS,isomer #1CN1C=NC2=C1N([Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C2=O2309.3Semi standard non polar33892256
9-Methylxanthine,2TBDMS,isomer #1CN1C=NC2=C1N([Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C2=O2503.3Standard non polar33892256
9-Methylxanthine,2TBDMS,isomer #1CN1C=NC2=C1N([Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C2=O2491.9Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 9-Methylxanthine GC-MS (Non-derivatized) - 70eV, Positivesplash10-00rj-4900000000-14c9b93c2a0a573bb5a52017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 9-Methylxanthine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 9-Methylxanthine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 9-Methylxanthine 20V, Negative-QTOFsplash10-0006-9200000000-b6abb15ab6e35e2289782021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 9-Methylxanthine 10V, Negative-QTOFsplash10-014i-3900000000-79a4c3d1ed77bec280132021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 9-Methylxanthine 30V, Negative-QTOFsplash10-0006-9000000000-2f53c894eb036b2baef62021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 9-Methylxanthine 40V, Negative-QTOFsplash10-0006-9000000000-466822a9d8f10adc15772021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 9-Methylxanthine 0V, Positive-QTOFsplash10-014i-0900000000-e40bb3a6f8a43919e5842021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 9-Methylxanthine 30V, Positive-QTOFsplash10-0006-9500000000-d153e1e54fadd31e75022021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 9-Methylxanthine 0V, Positive-QTOFsplash10-014i-0900000000-a8c2d37edc47b03668b72021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 9-Methylxanthine 10V, Positive-QTOFsplash10-014i-0900000000-16767a506e30f53c64cd2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 9-Methylxanthine 30V, Positive-QTOFsplash10-0fl3-9700000000-5a53919333c21ac6d0102021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 9-Methylxanthine 10V, Positive-QTOFsplash10-014i-0900000000-f64facd72b87d9b945b32021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 9-Methylxanthine 10V, Positive-QTOFsplash10-014i-0900000000-86e2afeaee08135cc56f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 9-Methylxanthine 20V, Positive-QTOFsplash10-0fk9-1900000000-e8e39324a58bcd907ad72021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 9-Methylxanthine 40V, Positive-QTOFsplash10-0006-9000000000-56a793d03fe5f580ac842021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 9-Methylxanthine 30V, Positive-QTOFsplash10-0fl3-9500000000-7abf024fb291dbcf2b322021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9-Methylxanthine 10V, Negative-QTOFsplash10-014i-0900000000-527a1e5ee8d3273d9ff12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9-Methylxanthine 20V, Negative-QTOFsplash10-0006-9400000000-31977135b3d4c64c4cef2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9-Methylxanthine 40V, Negative-QTOFsplash10-0006-9100000000-d178774b5036960a191b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9-Methylxanthine 10V, Negative-QTOFsplash10-014i-0900000000-d5b4655ae02ddbadcfc02021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9-Methylxanthine 20V, Negative-QTOFsplash10-014l-3900000000-a327a04048c667f854b62021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9-Methylxanthine 40V, Negative-QTOFsplash10-0006-9000000000-b279255d0a190f1ac3a42021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9-Methylxanthine 10V, Positive-QTOFsplash10-014i-0900000000-3641a8cdf2a03f895e622016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9-Methylxanthine 20V, Positive-QTOFsplash10-01b9-0900000000-90b7792d6bd0a62afc722016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9-Methylxanthine 40V, Positive-QTOFsplash10-006t-9600000000-aeed19861a80e9815e162016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9-Methylxanthine 10V, Positive-QTOFsplash10-014i-0900000000-d3632c2d43dc7c3c5d2b2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9-Methylxanthine 20V, Positive-QTOFsplash10-014i-0900000000-4eb2c7c6361ac0aedfac2021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX labView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedAdult (>18 years old)BothAsthma details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothAsthma details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkXanthine
METLIN IDNot Available
PubChem Compound70975
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Henderson-Smart DJ, Steer P: Methylxanthine treatment for apnea in preterm infants. Cochrane Database Syst Rev. 2001;(3):CD000140. [PubMed:11686952 ]
  2. Chapman RA, Leoty C: Which of caffeine's chemical relatives are able to evoke contractures in mammalian heart? Recent Adv Stud Cardiac Struct Metab. 1975;7:425-30. [PubMed:1226453 ]